Control over Excited State Intramolecular Proton Transfer and Photoinduced Tautomerization: Influence of the Hydrogen‐Bond Geometry |
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Authors: | Giovanny A Parada Dr Todd F Markle Dr Starla D Glover Prof?Dr Leif Hammarström Dr Sascha Ott Dr Burkhard Zietz |
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Institution: | 1. Department of Chemistry, ?ngstr?m Laboratories, Uppsala University, Box 523, 751 20 Uppsala (Sweden);2. Department of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520 (USA) |
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Abstract: | The influence of H‐bond geometry on the dynamics of excited state intramolecular proton transfer (ESIPT) and photoinduced tautomerization in a series of phenol‐quinoline compounds is investigated. Control over the proton donor–acceptor distance (dDA) and dihedral angle between the proton donor–acceptor subunits is achieved by introducing methylene backbone straps of increasing lengths to link the phenol and quinoline. We demonstrate that a long dDA correlates with a higher barrier for ESIPT, while a large dihedral angle opens highly efficient deactivation channels after ESIPT, preventing the formation of the fully relaxed tautomer photoproduct. |
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Keywords: | excited state fluorescence hydrogen bonds intramolecular proton transfer phenols tautomerism |
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